Dyes and process of dyeing.



wherein R means an aromatic radical such No Drawing.

UNITED STATES PATENT 01mm JOSEPH FLACI-ISLAENDER AND PAUL GEORG LIST, OFLEV'ERKUSEN, NEAR COLOGNE,

GERMANY, ASSIGNORS TO SYNTHETIC PAT CORPORATION OF NEW YORK.

' pounds of aromatic amins containing no sulfonic groups with thehydro-alpha-naphthalids of 2.8-oxynaphthoic acid which can be obtainedby condensing the 2.3-oxynaphthoio acid with hydro-alpha-naphthylaminese. g. dihydroor tetrahydro-alphanaphthylamin. The new dyes having mostprobably the following general formula:

as phenyl, naphthyl, and substitution products thereof, etc., asstanding for more than 7 hydrogens. I

The new dyes are after being dried and pulverized dark powders solublein concentrated sulfuricacid. Yielding upon reduction with tin andhydrochloric acid an aromatic amin and a hydro-alpha-naphthalid of-amino-2-oxy-3-naphthoic acid. They dye the fiber from orange to red toblue to black shades. The dyes may also be produced on the fiber.

In order to illustrate the new process more fully the following exampleis given, the

parts being by weight: 15.2 parts of para nitro-o-toluidin (CH5: NH NO 12 4) are dissolved in 37 parts of a 30 per cent. hydrochloric acid andwater. The dissolved base is then diazotized with the aid of? parts .ofsodium nitrite and the resulting solution is introduced into an aqueoussus- Specification of Letters Patent.

. red flakes.

NTS 00., mo, OF NEW YORK, N. Y., A

Patented Feb. 13, 1917.

Application filed July 29, 1916. Serial No. 111,998.

pension of 31.7 parts of tetra-hydrO-alphanaphthalid of the2.3-oxynaphthoic acid containing 27 parts of sodium acetate. Theresulting dyestuifseparates in the shape of When the formation of thedye is complete it is filtered off, washed until neutral and dried. Itis after being dried and pulverized a dark red powder soluble inconcentrated sulfuric acid with a red coloration. It has most probablythe formula Upon reduction with tin and hydrochloric acid it is split upinto diaminotoluene and the tetrahydro-alpha-naphthalid of the lam1no2-oxy-3-naphthoic acid.

Production of the dyes-W77 on the fiber.-

The cotton goods are impregnated with the following solution: 14.4 gramsof the tetrahydro-al ha-naphthalid of the 2.3-oxynaphthoic acid arestirred up with 12 cubic centimeters of caustic soda lye of 30 B. and 25cubic centimeters of Turkey red oil to a paste, 500 cubic centimeters ofboiling water are added, heated to boiling and filled up to 1000 cubiccentimeters. The cotton is treated in this solution during 15 minutes at'70 C., wrung out, and treated with a diazo com pound obtained in thefollowing way: 17 grams 'of 5-nitro-2-anisidin are stirred up with 30cubic centimeters of concentrated hydrochloric acid 22 B. Hot water isadded until all be dissolved. Subsequently the solution is cooled withice and the amln The following shades can thus be obta ined a From6-nitro-2-to1uidin Orange 4-nitro-2-anisidin- Scarlet 2.4-dichloroanilinOrange 2.5-dichloroanilin Grange beta-naphthylamin Bluish-redl-ziminoanthraquinone- Yellowish-red Q-aminoanthraquinone .Redp-nitranilin Red m-nitro-p-toluidin ;-Bordeaux p-nitro-o-toluidinScarlet 2-nitro-4c-toluidin Bluish-red o-nitranilin Bluish-reddianisidin -Blue tolidin.. ,Blue-black We claim 1. As new articles ofmanufacture the azo dyes, which 'may be obtained from diazo compoundsand a hydro-alpha-naphthalid of 2.3-oxynaphthoic acid having mostprobably the following general formula:

' substantially as described.

2. As new articles of'manufacture the azo dyes having most probably thefollowing general formula: I

' 'RN=N-R R meaning a nitro-aryl of the benzene series and R standingfor the radical of a 2.3- oXynaphthoyl-hydronaphthalid having the azogroup in the 1-position, which dyes are after being dried and pulverizeddark powders soluble in concentrated sulfuric acid and dyeing cottonreddish shades fast to washing, substantially-as described.

3. As a new article of manufacture the azo dye which may be obtainedfrom diazotized para-nitro-ortho-toluidin and thetetrahydro-alpha-naphthalin of 2.3-oxynaphthoic acid having mostprobably the formula:

which is after being dried and pulverized a dark red powder soluble inconcentrated sulfuric acid with a red coloration; yielding uponreduction with tin and hydrochloric acid diaminotoluene and thetetrahydroalpha-naphthalid of the 2.3-oxynaphthoic acid; and dyeingcotton red shades, substantially as described.

4. Production of azo dyes on the fiber consisting in impregnating thefiber with a solution of a hydro-alpha-naphthalid of the 2.3-oxynaphthoic acid and treating it with a diazo compound, substantiallyas described. In testimony whereof we have hereunto set our hands in thepresence of two subscribing witnesses.

JOSEPH rticnstninnsii. 1,. a] r m. GEORG LIST. [n.a]

Witnesses:

HELEN Norm, Armani F. Norm.

